4-Amino-N-(2,3-dichloro­phen­yl)benzene­sulfonamide

In the crystal structure of the title compound, C₁₂H₁₀Cl₂N₂O₂S, there are two independent mol­ecules in the asymmetric unit. Hydrogen bonds between NH₂ and SO₂ groups link molecules into layers, which inter­act with each other only by van der Waals forces

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.080
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O2      ..       3.02 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22A   ..  O21     ..       2.94 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C12 H10 Cl2 N2 O2 S

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1989); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (reference?); software used to prepare material for publication: CIFTAB (reference?).

4-Amino-N-(2,3-dichlorophenyl)benzenesulfonamide

Crystal data

C12H10Cl2N2O2S	F(000) = 648
Mr = 317.18	Dx = 1.568 Mg m^−3
Triclinic, P1	Melting point: 454.3(2) K
a = 7.4700 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.613 (1) Å	Cell parameters from 35 reflections
c = 14.548 (1) Å	θ = 5–12°
α = 110.91 (1)°	µ = 0.64 mm^−1
β = 90.51 (1)°	T = 200 K
γ = 102.42 (1)°	Prism, colourless
V = 1343.6 (2) Å^3	0.4 × 0.2 × 0.2 mm
Z = 4

Data collection

Siemens P4 diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = −1→8
ω–2θ scans	k = −15→14
5502 measured reflections	l = −17→17
4499 independent reflections	3 standard reflections every 2 reflections
4325 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0359P)^2 + 0.8502P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
4499 reflections	Δρmax = 0.31 e Å^−3
362 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0131 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.08868 (6)	0.17279 (3)	0.30762 (3)	0.02018 (12)
Cl1	−0.35142 (6)	0.35743 (4)	0.37594 (4)	0.03067 (13)
Cl2	−0.26169 (7)	0.60192 (4)	0.39889 (4)	0.04035 (15)
O1	−0.02185 (18)	0.07327 (10)	0.30945 (9)	0.0259 (3)
O2	0.27445 (17)	0.20842 (11)	0.35291 (9)	0.0263 (3)
N1	−0.0283 (2)	0.26300 (13)	0.36202 (11)	0.0229 (3)
N2	0.1022 (2)	0.12808 (13)	−0.11187 (11)	0.0254 (3)
C1	0.0953 (2)	0.16562 (14)	0.18517 (12)	0.0204 (4)
C2	−0.0697 (2)	0.12792 (14)	0.12399 (13)	0.0225 (4)
H2	−0.1809	0.1114	0.1496	0.027*
C3	−0.0672 (2)	0.11534 (14)	0.02583 (13)	0.0225 (4)
H3	−0.1770	0.0904	−0.0147	0.027*
C4	0.1003 (3)	0.13999 (14)	−0.01325 (13)	0.0212 (4)
C5	0.2642 (2)	0.18018 (15)	0.04933 (13)	0.0246 (4)
H5	0.3753	0.1988	0.0245	0.030*
C6	0.2616 (2)	0.19229 (15)	0.14784 (13)	0.0250 (4)
H6	0.3709	0.2182	0.1889	0.030*
C7	0.0135 (2)	0.37062 (14)	0.36564 (12)	0.0215 (4)
C8	−0.1280 (2)	0.42513 (15)	0.37484 (12)	0.0222 (4)
C9	−0.0885 (3)	0.53259 (15)	0.38279 (13)	0.0252 (4)
C10	0.0889 (3)	0.58607 (16)	0.37850 (14)	0.0292 (4)
H10	0.1143	0.6576	0.3829	0.035*
C11	0.2270 (3)	0.53155 (16)	0.36767 (15)	0.0311 (4)
H11	0.3466	0.5667	0.3640	0.037*
C12	0.1919 (3)	0.42551 (16)	0.36219 (14)	0.0281 (4)
H12	0.2880	0.3907	0.3562	0.034*
S21	0.34092 (6)	−0.16528 (4)	0.19697 (3)	0.02337 (13)
Cl21	−0.22476 (7)	−0.35848 (4)	0.15513 (4)	0.03547 (14)
Cl22	−0.29998 (7)	−0.60365 (4)	0.13093 (4)	0.04141 (15)
O21	0.30338 (19)	−0.06822 (11)	0.19214 (10)	0.0313 (3)
O22	0.50393 (18)	−0.19703 (12)	0.15791 (10)	0.0324 (3)
N21	0.1609 (2)	−0.26069 (13)	0.13586 (11)	0.0242 (3)
N22	0.3854 (2)	−0.11132 (14)	0.61912 (12)	0.0276 (4)
C21	0.3486 (2)	−0.15571 (14)	0.32033 (13)	0.0223 (4)
C22	0.2263 (3)	−0.10562 (16)	0.38138 (14)	0.0272 (4)
H22	0.1369	−0.0820	0.3556	0.033*
C23	0.2383 (3)	−0.09120 (15)	0.48017 (14)	0.0274 (4)
H23	0.1559	−0.0583	0.5209	0.033*
C24	0.3736 (2)	−0.12579 (14)	0.51956 (13)	0.0222 (4)
C25	0.4928 (3)	−0.17778 (15)	0.45735 (14)	0.0264 (4)
H25	0.5810	−0.2027	0.4827	0.032*
C26	0.4809 (3)	−0.19254 (15)	0.35830 (13)	0.0257 (4)
H26	0.5611	−0.2270	0.3171	0.031*
C27	0.1299 (3)	−0.36903 (15)	0.13061 (12)	0.0235 (4)
C28	−0.0471 (3)	−0.42434 (15)	0.13695 (13)	0.0241 (4)
C29	−0.0795 (3)	−0.53256 (15)	0.12685 (13)	0.0272 (4)
C30	0.0619 (3)	−0.58495 (17)	0.11441 (15)	0.0337 (5)
H30	0.0397	−0.6566	0.1095	0.040*
C31	0.2365 (3)	−0.52976 (17)	0.10936 (16)	0.0370 (5)
H31	0.3329	−0.5645	0.1014	0.044*
C32	0.2711 (3)	−0.42338 (17)	0.11590 (15)	0.0321 (4)
H32	0.3895	−0.3880	0.1104	0.039*
H1	−0.131 (3)	0.2370 (19)	0.3681 (17)	0.035*
H2A	0.019 (3)	0.075 (2)	−0.1514 (17)	0.035*
H2B	0.209 (3)	0.1316 (19)	−0.1340 (17)	0.035*
H21	0.070 (3)	−0.2365 (19)	0.1320 (17)	0.035*
H22A	0.483 (3)	−0.1184 (19)	0.6416 (17)	0.035*
H22B	0.337 (3)	−0.062 (2)	0.6560 (17)	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0216 (2)	0.0209 (2)	0.0187 (2)	0.00647 (18)	0.00095 (16)	0.00723 (17)
Cl1	0.0174 (2)	0.0302 (3)	0.0442 (3)	0.00384 (19)	0.00067 (18)	0.0145 (2)
Cl2	0.0344 (3)	0.0317 (3)	0.0575 (3)	0.0164 (2)	−0.0006 (2)	0.0147 (2)
O1	0.0320 (7)	0.0224 (7)	0.0251 (6)	0.0071 (6)	0.0046 (5)	0.0106 (5)
O2	0.0230 (7)	0.0314 (7)	0.0252 (6)	0.0088 (6)	−0.0021 (5)	0.0099 (5)
N1	0.0203 (8)	0.0210 (8)	0.0262 (8)	0.0041 (6)	0.0043 (6)	0.0077 (6)
N2	0.0288 (8)	0.0242 (9)	0.0212 (8)	0.0036 (7)	0.0024 (7)	0.0076 (6)
C1	0.0248 (9)	0.0186 (9)	0.0188 (8)	0.0064 (7)	0.0020 (7)	0.0074 (7)
C2	0.0204 (9)	0.0216 (9)	0.0259 (9)	0.0043 (7)	0.0025 (7)	0.0095 (7)
C3	0.0228 (9)	0.0184 (9)	0.0247 (9)	0.0021 (7)	−0.0034 (7)	0.0079 (7)
C4	0.0282 (9)	0.0134 (8)	0.0225 (8)	0.0054 (7)	0.0012 (7)	0.0071 (7)
C5	0.0205 (9)	0.0257 (10)	0.0270 (9)	0.0038 (7)	0.0051 (7)	0.0098 (8)
C6	0.0197 (9)	0.0274 (10)	0.0248 (9)	0.0032 (8)	−0.0022 (7)	0.0075 (7)
C7	0.0229 (9)	0.0216 (9)	0.0182 (8)	0.0042 (7)	0.0001 (7)	0.0058 (7)
C8	0.0182 (8)	0.0239 (10)	0.0212 (8)	0.0019 (7)	−0.0013 (6)	0.0061 (7)
C9	0.0262 (9)	0.0243 (10)	0.0247 (9)	0.0091 (8)	−0.0025 (7)	0.0066 (7)
C10	0.0317 (10)	0.0217 (10)	0.0304 (10)	0.0019 (8)	−0.0026 (8)	0.0077 (8)
C11	0.0219 (9)	0.0276 (11)	0.0401 (11)	−0.0015 (8)	0.0011 (8)	0.0123 (9)
C12	0.0211 (9)	0.0275 (11)	0.0347 (10)	0.0076 (8)	0.0030 (8)	0.0093 (8)
S21	0.0210 (2)	0.0257 (3)	0.0222 (2)	0.00013 (18)	−0.00040 (17)	0.01065 (18)
Cl21	0.0251 (2)	0.0304 (3)	0.0545 (3)	0.0101 (2)	0.0102 (2)	0.0177 (2)
Cl22	0.0361 (3)	0.0308 (3)	0.0547 (3)	−0.0023 (2)	0.0015 (2)	0.0186 (2)
O21	0.0357 (8)	0.0270 (7)	0.0308 (7)	−0.0017 (6)	−0.0052 (6)	0.0153 (6)
O22	0.0220 (7)	0.0434 (9)	0.0303 (7)	0.0027 (6)	0.0054 (5)	0.0145 (6)
N21	0.0210 (8)	0.0233 (9)	0.0273 (8)	0.0037 (7)	−0.0040 (6)	0.0091 (6)
N22	0.0281 (9)	0.0302 (9)	0.0244 (8)	0.0044 (7)	−0.0007 (7)	0.0112 (7)
C21	0.0218 (9)	0.0222 (9)	0.0226 (9)	0.0014 (7)	−0.0014 (7)	0.0099 (7)
C22	0.0241 (9)	0.0320 (11)	0.0289 (10)	0.0083 (8)	0.0007 (7)	0.0142 (8)
C23	0.0274 (10)	0.0289 (11)	0.0285 (9)	0.0094 (8)	0.0064 (8)	0.0118 (8)
C24	0.0218 (9)	0.0182 (9)	0.0244 (9)	−0.0027 (7)	−0.0015 (7)	0.0094 (7)
C25	0.0233 (9)	0.0276 (10)	0.0295 (10)	0.0057 (8)	−0.0031 (7)	0.0120 (8)
C26	0.0244 (9)	0.0247 (10)	0.0273 (9)	0.0069 (8)	0.0017 (7)	0.0081 (8)
C27	0.0254 (9)	0.0235 (10)	0.0192 (8)	0.0043 (8)	−0.0028 (7)	0.0060 (7)
C28	0.0247 (9)	0.0248 (10)	0.0228 (9)	0.0084 (8)	0.0000 (7)	0.0071 (7)
C29	0.0296 (10)	0.0237 (10)	0.0254 (9)	0.0015 (8)	−0.0031 (7)	0.0082 (8)
C30	0.0414 (12)	0.0239 (11)	0.0341 (11)	0.0088 (9)	−0.0048 (9)	0.0080 (8)
C31	0.0350 (11)	0.0320 (12)	0.0450 (12)	0.0167 (9)	−0.0035 (9)	0.0105 (9)
C32	0.0234 (10)	0.0327 (11)	0.0383 (11)	0.0073 (8)	−0.0018 (8)	0.0105 (9)

Geometric parameters (Å, º)

S1—O2	1.4357 (13)	S21—O21	1.4335 (14)
S1—O1	1.4363 (14)	S21—O22	1.4338 (14)
S1—N1	1.6363 (16)	S21—N21	1.6400 (16)
S1—C1	1.7507 (17)	S21—C21	1.7519 (17)
Cl1—C8	1.7276 (18)	Cl21—C28	1.7274 (18)
Cl2—C9	1.7299 (18)	Cl22—C29	1.735 (2)
N1—C7	1.412 (2)	N21—C27	1.417 (2)
N1—H1	0.79 (2)	N21—H21	0.82 (2)
N2—C4	1.386 (2)	N22—C24	1.390 (2)
N2—H2A	0.86 (3)	N22—H22A	0.83 (3)
N2—H2B	0.86 (2)	N22—H22B	0.84 (2)
C1—C6	1.389 (3)	C21—C26	1.391 (3)
C1—C2	1.399 (2)	C21—C22	1.392 (3)
C2—C3	1.377 (2)	C22—C23	1.379 (3)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.403 (3)	C23—C24	1.400 (3)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.401 (3)	C24—C25	1.393 (3)
C5—C6	1.384 (3)	C25—C26	1.381 (3)
C5—H5	0.9300	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—C12	1.391 (3)	C27—C32	1.391 (3)
C7—C8	1.398 (3)	C27—C28	1.395 (3)
C8—C9	1.390 (3)	C28—C29	1.394 (3)
C9—C10	1.381 (3)	C29—C30	1.376 (3)
C10—C11	1.375 (3)	C30—C31	1.375 (3)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.383 (3)	C31—C32	1.383 (3)
C11—H11	0.9300	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300
O2—S1—O1	118.26 (8)	O21—S21—O22	118.74 (9)
O2—S1—N1	109.94 (8)	O21—S21—N21	104.51 (8)
O1—S1—N1	104.31 (8)	O22—S21—N21	108.70 (8)
O2—S1—C1	107.97 (8)	O21—S21—C21	108.99 (8)
O1—S1—C1	109.34 (8)	O22—S21—C21	107.39 (8)
N1—S1—C1	106.43 (8)	N21—S21—C21	108.11 (8)
C7—N1—S1	124.90 (13)	C27—N21—S21	123.94 (13)
C7—N1—H1	118.1 (17)	C27—N21—H21	117.8 (16)
S1—N1—H1	113.1 (17)	S21—N21—H21	112.2 (16)
C4—N2—H2A	115.0 (15)	C24—N22—H22A	115.9 (16)
C4—N2—H2B	115.2 (15)	C24—N22—H22B	115.4 (16)
H2A—N2—H2B	113 (2)	H22A—N22—H22B	117 (2)
C6—C1—C2	120.33 (16)	C26—C21—C22	120.27 (16)
C6—C1—S1	120.87 (14)	C26—C21—S21	120.62 (14)
C2—C1—S1	118.75 (13)	C22—C21—S21	119.03 (14)
C3—C2—C1	119.93 (16)	C23—C22—C21	119.78 (17)
C3—C2—H2	120.0	C23—C22—H22	120.1
C1—C2—H2	120.0	C21—C22—H22	120.1
C2—C3—C4	120.29 (16)	C22—C23—C24	120.37 (17)
C2—C3—H3	119.9	C22—C23—H23	119.8
C4—C3—H3	119.9	C24—C23—H23	119.8
N2—C4—C5	120.61 (17)	N22—C24—C25	120.32 (17)
N2—C4—C3	120.13 (16)	N22—C24—C23	120.32 (17)
C5—C4—C3	119.22 (16)	C25—C24—C23	119.33 (16)
C6—C5—C4	120.44 (16)	C26—C25—C24	120.39 (17)
C6—C5—H5	119.8	C26—C25—H25	119.8
C4—C5—H5	119.8	C24—C25—H25	119.8
C5—C6—C1	119.76 (16)	C25—C26—C21	119.83 (17)
C5—C6—H6	120.1	C25—C26—H26	120.1
C1—C6—H6	120.1	C21—C26—H26	120.1
C12—C7—C8	118.48 (17)	C32—C27—C28	118.77 (17)
C12—C7—N1	122.30 (16)	C32—C27—N21	121.48 (17)
C8—C7—N1	119.21 (16)	C28—C27—N21	119.72 (16)
C9—C8—C7	120.09 (16)	C29—C28—C27	119.76 (17)
C9—C8—Cl1	120.64 (14)	C29—C28—Cl21	120.66 (15)
C7—C8—Cl1	119.28 (14)	C27—C28—Cl21	119.58 (14)
C10—C9—C8	120.93 (17)	C30—C29—C28	121.01 (18)
C10—C9—Cl2	118.80 (15)	C30—C29—Cl22	118.63 (15)
C8—C9—Cl2	120.27 (14)	C28—C29—Cl22	120.36 (15)
C11—C10—C9	118.76 (18)	C31—C30—C29	119.00 (19)
C11—C10—H10	120.6	C31—C30—H30	120.5
C9—C10—H10	120.6	C29—C30—H30	120.5
C10—C11—C12	121.35 (18)	C30—C31—C32	121.10 (19)
C10—C11—H11	119.3	C30—C31—H31	119.5
C12—C11—H11	119.3	C32—C31—H31	119.5
C11—C12—C7	120.36 (18)	C31—C32—C27	120.31 (19)
C11—C12—H12	119.8	C31—C32—H32	119.8
C7—C12—H12	119.8	C27—C32—H32	119.8
O2—S1—N1—C7	61.42 (16)	O21—S21—N21—C27	−173.03 (15)
O1—S1—N1—C7	−170.83 (14)	O22—S21—N21—C27	59.24 (17)
C1—S1—N1—C7	−55.27 (16)	C21—S21—N21—C27	−57.04 (17)
O2—S1—C1—C6	−0.04 (18)	O21—S21—C21—C26	−139.32 (15)
O1—S1—C1—C6	−129.93 (15)	O22—S21—C21—C26	−9.49 (18)
N1—S1—C1—C6	117.95 (16)	N21—S21—C21—C26	107.64 (16)
O2—S1—C1—C2	177.19 (13)	O21—S21—C21—C22	37.43 (17)
O1—S1—C1—C2	47.30 (16)	O22—S21—C21—C22	167.26 (15)
N1—S1—C1—C2	−64.82 (16)	N21—S21—C21—C22	−75.61 (17)
C6—C1—C2—C3	1.1 (3)	C26—C21—C22—C23	0.9 (3)
S1—C1—C2—C3	−176.11 (13)	S21—C21—C22—C23	−175.85 (15)
C1—C2—C3—C4	0.1 (3)	C21—C22—C23—C24	0.6 (3)
C2—C3—C4—N2	−179.46 (16)	C22—C23—C24—N22	−179.93 (17)
C2—C3—C4—C5	−1.7 (3)	C22—C23—C24—C25	−1.9 (3)
N2—C4—C5—C6	179.78 (17)	N22—C24—C25—C26	179.78 (17)
C3—C4—C5—C6	2.0 (3)	C23—C24—C25—C26	1.7 (3)
C4—C5—C6—C1	−0.8 (3)	C24—C25—C26—C21	−0.3 (3)
C2—C1—C6—C5	−0.8 (3)	C22—C21—C26—C25	−1.1 (3)
S1—C1—C6—C5	176.38 (14)	S21—C21—C26—C25	175.65 (14)
S1—N1—C7—C12	−28.1 (2)	S21—N21—C27—C32	−43.0 (2)
S1—N1—C7—C8	153.10 (14)	S21—N21—C27—C28	139.22 (15)
C12—C7—C8—C9	−1.6 (3)	C32—C27—C28—C29	−1.1 (3)
N1—C7—C8—C9	177.24 (16)	N21—C27—C28—C29	176.81 (16)
C12—C7—C8—Cl1	178.28 (13)	C32—C27—C28—Cl21	−179.96 (14)
N1—C7—C8—Cl1	−2.9 (2)	N21—C27—C28—Cl21	−2.1 (2)
C7—C8—C9—C10	2.1 (3)	C27—C28—C29—C30	2.5 (3)
Cl1—C8—C9—C10	−177.72 (14)	Cl21—C28—C29—C30	−178.63 (15)
C7—C8—C9—Cl2	−177.55 (13)	C27—C28—C29—Cl22	−178.12 (14)
Cl1—C8—C9—Cl2	2.6 (2)	Cl21—C28—C29—Cl22	0.8 (2)
C8—C9—C10—C11	−1.0 (3)	C28—C29—C30—C31	−1.7 (3)
Cl2—C9—C10—C11	178.73 (15)	Cl22—C29—C30—C31	178.87 (16)
C9—C10—C11—C12	−0.7 (3)	C29—C30—C31—C32	−0.4 (3)
C10—C11—C12—C7	1.3 (3)	C30—C31—C32—C27	1.8 (3)
C8—C7—C12—C11	−0.1 (3)	C28—C27—C32—C31	−1.0 (3)
N1—C7—C12—C11	−178.87 (17)	N21—C27—C32—C31	−178.88 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N22^i	0.79 (2)	2.33 (3)	3.083 (2)	160 (2)
N2—H2a···O1^ii	0.86 (3)	2.47 (2)	3.126 (2)	134 (2)
N2—H2a···O21^ii	0.86 (3)	2.45 (2)	3.066 (2)	130 (2)
N2—H2b···O22^iii	0.86 (2)	2.22 (3)	3.047 (2)	161 (2)
N21—H21···N2^ii	0.82 (2)	2.25 (3)	3.034 (2)	160 (2)
N22—H22a···O2^iv	0.83 (2)	2.41 (3)	3.190 (2)	156 (2)
N22—H22a···O21^iv	0.83 (2)	2.94 (2)	3.401 (2)	117 (2)
N22—H22b···O1^i	0.84 (2)	2.40 (2)	2.999 (2)	129 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) −x+1, −y, −z+1.